2,2'-bis(hexahydropyrimidine) | 122763-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2,2'-bis(hexahydropyrimidine)
• 英文别名: 2-(1,3-Diazinan-2-yl)-1,3-diazinane
• CAS: 122763-13-7
• 化学式: C₈H₁₈N₄
• 分子量: 170.258
• InChiKey: RHNGIIMOVOYDKG-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  302.1±10.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-bis(hexahydropyrimidine) 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以84%的产率得到2,2'-bis(1,3-dinitrosohexahydropyrimidine)
  参考文献：
  名称：

  1,3-dinitroso-, 1-nitroso-3-nitro-, and 1,3-dinitro-1,3-diazacycloalkanes. A multinuclear NMR study

  摘要：

  通过 1H、13C 和 15N NMR 光谱研究了一系列五元、六元和七元 1,3-二亚硝基、1-亚硝基-3-硝基和 1,3-二硝基-1,3-二氮杂环烷烃。亚硝胺基团的受阻旋转导致了旋转异构体的存在。旋转异构体的相对数量取决于亚硝基与分子其余部分之间的立体和静电相互作用以及环的大小。

  DOI：

  10.1002/mrc.1260260202
• 作为产物：
  描述：

  草酸醛 、 1,3-丙二胺 以 水 为溶剂， 反应 3.0h， 以45%的产率得到2,2'-bis(hexahydropyrimidine)
  参考文献：
  名称：

  Jazwinski, Jaroslaw; Kolinski, Ryszard A., Bulletin of the Polish Academy of Sciences: Chemistry, 1988, vol. 36, # 5-6, p. 215 - 220

  摘要：

  DOI：

文献信息

• 1,3-dinitroso-, 1-nitroso-3-nitro-, and 1,3-dinitro-1,3-diazacycloalkanes. A multinuclear NMR study
  作者：Rodney L. Willer、Donald W. Moore

  DOI：10.1002/mrc.1260260202

  日期：1988.2

  A series of five-, six-, and seven-membered 1,3-dinitroso-, 1-nitroso-3-nitro-, and 1,3-dinitro-1,3-diazacycloalkanes were investigated by 1H, 13C, and 15N NMR spectroscopy. Hindered rotation of the nitrosamine group leads to the existence of rotational isomers. The relative populations of rotamer forms are determined by steric and electrostatic interactions between nitroso groups and the remainder of the molecule, and by the size of the ring.

  通过 1H、13C 和 15N NMR 光谱研究了一系列五元、六元和七元 1,3-二亚硝基、1-亚硝基-3-硝基和 1,3-二硝基-1,3-二氮杂环烷烃。亚硝胺基团的受阻旋转导致了旋转异构体的存在。旋转异构体的相对数量取决于亚硝基与分子其余部分之间的立体和静电相互作用以及环的大小。
• Electronegatively substituted pyrimidines and intermediates leading to RNFX
  申请人：——

  公开号：US20020007063A1

  公开（公告）日：2002-01-17

  Calculated performance improvements are expected from a particularly new class of compounds, geminal-bis(difluoramino)-substituted heterocyclic nitramines, when formulated into explosives and propellants. This invention involves novel and nonintuitive methods for the preparation of certain derivatives of 2,2-bis(difluoramino)-N-nitro-1,3-propanediamine which are suitable precursors leading to 5,5-bis(difluoramino)hexahydro-1,3-dinitropyrimidine (RNFX). The invention also involves novel and nonintuitive methods for the preparation of RNFX, a specific member of a general class of compounds with the substructure 2,2-bis(difluoramino)-N-nitro-1,3-propanediamine. RNFX is produced by the use of key intermediates, including tetrahydropyrimidin-5(4H)-ones, which allow formation of the target structural subcomponent, 2,2-bis(difluoramino)-N-nitro-1,3-propanediamine, and a more specific substructure of 2,2-bis(difluoramino)-N,N′-dinitro-1,3-propanediamine. In addition, this invention involves 5,5-bis(difluoramino)hexahydropyrimidine derivatives, related geminal-bis(difluoramino)alkylene derivatives, and novel precursors to these new derivatives, by the use of certain novel key intermediates.

  预计从一种特别新的化合物类别——双（二氟氨基）取代的杂环硝胺基化合物（geminal-bis(difluoramino)-substituted heterocyclic nitramines）中，当制成炸药和推进剂时，将获得计算性能改进。本发明涉及制备2,2-双（二氟氨基）-N-硝基-1,3-丙二胺的某些衍生物的新颖和非直观方法，这些衍生物是导致5,5-双（二氟氨基）六氢-1,3-二硝基嘧啶（RNFX）的合适前体。本发明还涉及制备RNFX的新颖和非直观方法，RNFX是具有亚结构2,2-双（二氟氨基）-N-硝基-1,3-丙二胺的化合物类别的特定成员。通过使用关键中间体，包括四氢嘧啶-5（4H）-酮，可以形成目标结构亚组分2,2-双（二氟氨基）-N-硝基-1,3-丙二胺，以及更具体的亚结构2,2-双（二氟氨基）-N,N'-二硝基-1,3-丙二胺。此外，本发明涉及5,5-双（二氟氨基）六氢嘧啶衍生物，相关的双（二氟氨基）烷基衍生物以及这些新衍生物的新前体，通过使用某些新的关键中间体。
• Jazwinski, Jaroslaw; Kolinski, Ryszard A., Bulletin of the Polish Academy of Sciences: Chemistry, 1988, vol. 36, # 5-6, p. 215 - 220
  作者：Jazwinski, Jaroslaw、Kolinski, Ryszard A.

  DOI：——

  日期：——
• Preparation and Stereochemistry of 1,4,8,11-Tetraazaperhydropyrene Derivatives from N,N'-Bis(3-aminopropyl)ethylenediamine
  作者：Tadashi Okawara、Hisashi Takaishi、Yoshinari Okamoto、Tetsuo Yamasaki、Mitsuru Furukawa

  DOI：10.3987/com-95-7038

  日期：——

  The reaction of N,N'-bis(3-aminopropyl) ethylenediamine (1) with glyoxal (2) in the presence of benzotriazole (3) afforded dibenzotriazoyltetraazaperhydropyrene (4), which was converted to polyazapolycycles (6), (13), (15), (16), and (19). The stereochemistry is discussed.
• Reactions of perhydro-2,2'-bipyrimidines with carbonyl compounds bearing .alpha.-carbonyl functionality
  作者：Donald C. Craig、Alan Doughty、Michael Kassiou、Malcolm G. MacIntosh、Roger W. Read

  DOI：10.1021/jo00073a039

  日期：1993.10

  Treatment of perhydro-2,2'-bipyrimidine (1) with glyoxal, glyoxylic acid, and ethyl glyoxylate in MeOH yields 10b,10c-trans-4,5,9,10-tetramethoxyperhydro-3a,5a,8a,10a-tetraazapyrene (5), 1,3-diazacyclohexane-2-carboxylic acid (9) and 10b,10c-trans-5,10-dimethoxyperhydro-3a,5a,8a,10a-tetraazapyrene-4,9-dione (10), respectively, while similar treatment of 5,5,5',5'-tetramethylperhydro-2,2'-bipyrimidine (2) with glyoxal gives an inseparable mixture of 10b,10c-trans-4,5,9,10-tetramethoxy-2,2,7,7-tetramethylperhydro-3a,5a,8a,10a-tetraazapyrene (7) and an isomeric substance and reaction with diethyl oxomalonate gives ethyl 4a,4b-trans-9-hydroxy-10-oxoperhydro-4,5,8a,10a-tetraazaphenanthrene-9-carbox ylate (12) or an unequal mixture of diethyl 10b,10c-trans-4,9-dihydroxy-5,10-dioxoperhydro-3a,5a,8a,10a-tetraazapyrene-4,9-dicarboxylate (13) and diethyl 10b,10c-trans-4,10-dihydroxy-5,9-dioxoperhydro-3a,5a,8a,10a-tetraazapyrene-4, 10-dicarboxylate (14), respectively, depending upon reaction conditions. The relative configuration of substituents in 5 is determined by NOE difference experiments, and the structure of 10 is confirmed by X-ray crystallography. Formation of these compounds represents a departure from the mode of condensation of perhydro-2,2'-bipyrimidines with simple aldehydes and ketones.